


Enter Night

by LSeale



Category: Original Work
Genre: Abusive Relationships, Cock Cages, Cock Slapping, Come Shot, Conditioning, Deepthroating, Drugged Sex, Emotional Manipulation, Face-Fucking, Facials, Gags, M/M, Medication, Non-Consensual Somnophilia, Non-Consensual Voyeurism, Object Insertion, Painful Sex, Somnophilia, Spanking, Verbal Humiliation
Language: English
Status: In-Progress
Published: 2016-11-14
Updated: 2018-03-12
Packaged: 2018-08-30 22:36:41
Rating: Explicit
Warnings: Rape/Non-Con
Chapters: 2
Words: 14,081
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/8551876
Author URL: https://archiveofourown.org/users/LSeale/pseuds/LSeale
Summary: Max will freely admit to most people who ask that he's an asshole. This didn't stop him from bagging Tommy, an eager-to-please college student who's a little too clingy for his own good. Tommy has to start taking sleeping medication to help with a sleep rhythm disorder. What he doesn't realize is that giving Max permission to take advantage of him while he's asleep needed to come with limits. Limits Tommy didn't set, and limits Max probably wouldn't have listened to anyway.





	1. Chapter 1

**Author's Note:**

> This story contains a depiction of a manipulative and abusive relationship where one partner's consent is disregarded. Full explanation of tags for this chapter can be found in the end notes.

Something had been bugging Tommy. Max didn't bring it up - mostly because things that bugged Tommy usually annoyed the fuck out of Max when he started explaining. Juvenile shit. Max had his own shit to worry about without hearing Tommy talk his ear off about his little undergrad friends and their bullshit problems.

Honestly, if Tommy didn't fuck so good, Max probably wouldn't have bothered stringing him along this much. He was sweet and a little dumb - or, not dumb, because he did say shit sometimes that Max couldn't even wrap his brain around, but too trusting. He also sucked cock like he was born to be on his knees, and Max couldn't say no to that, not when all he had to do was supply alcohol to their little dorm parties and occasionally give Tommy some cuddle time when he was feeling needy.

Which was now, apparently, because Tommy didn't do anything else but toe off his shoes and drop his bag before crawling on the couch with Max, molding himself up against Max's side. "Can I talk to you?"

Shit. When Tommy wanted to talk, it usually turned into a tedious rehash of his annoying tendency to want to _plan for the future_ , especially where Max was concerned. Max had a little bet running with himself, trying to figure out how many times he could rebuff Tommy's nebulous "when I graduate" plans before Tommy figured out Max was going to drop him like a hot rock when he graduated. A college kid who lived in a dorm and ate on a meal plan was one thing. Tommy on his own, newly graduated with no job? Max would have to support that, and that wasn't what Max was about.

Still, he wanted to keep Tommy on the string for a little while longer, so he switched the TV off. "What's up?"

Tommy squirmed. Max hated it when he did this more than when he did most other things. He'd say he wanted to talk, and then it took an hour to pry what he wanted to say out from his mouth. "I just... remember what I said last week, about how I've been feeling tired all the time?"

Vaguely. "Sure, baby. I told you if you wanted you didn't have to come over every night." It was true, he had - because Tommy was great to have around to fuck, but he got exhausting in large doses.

"Yeah but." Tommy shrugged, turning his face into Max's neck, and grinned into his skin. "I want to be here with you."

Max could have groaned. Instead, he looped his arm around Tommy's shoulders and skimmed his fingertips gently over Tommy's arm. "I appreciate that. But you've got to get enough sleep, and I don't mind."

"Well, maybe I won't have to, and we can do both." Tommy sat up, shifting around to face him on the couch. He was nervous - his big brown eyes kept darting away from Max's face to settle in Tommy's lap. "I went to the doctor. You know I didn't come over on Thursday last week? I was having a sleep study."

"A sleep study." Max had no idea where this was going and was trying to figure out whether he should even care. "What did they say?"

"Something about sleep phases, and how I'm not reaching the right one, or at least not staying there long enough - anyway, they gave me a prescription. For um, sleeping pills."

 _Sleeping pills_ , holy shit. Now Max was paying attention, and it was his turn to try and seem more casual than he really was. "You think it'll help?"

"The doctor said they should." Tommy shifted again, sucking his lip into his mouth to bite down on it, and if the thoughts starting to stir at the back of Max's mind hadn't been dirty before, they were now. "Thing is, I have to take it kind of early. Like, nine. Or else I might not wake up in time to go to class - these things are supposed to have me dead to the world for like ten hours."

Oh, hell, there went Max's heart rate. He casually turned on the couch, propping one leg up against the back cushions in a move that would hopefully hide the semi he was sporting. "That's kind of early." He put a little doubt in his voice, frowning. "I mean, you usually roll in around seven. That's barely enough time to eat, and then we wouldn't have time for-"

"-Sex. Yeah." Tommy was turning pink, in that really cute way he did where it crawled across his face from his cheeks to the bridge of his nose. "Not while I was awake, anyway."

Oh, _hell_. He couldn't have just said what Max thought he said - couldn't have just _handed that over_ on a silver platter. He- "Come again?"

"I mean." Tommy licked his lips. "I mean, if I'm going to be asleep, and the doctor says these pills are really going to knock me out, you could just... I mean, you could... do what you wanted."

Max took it back. Sometimes things that bugged Tommy didn't turn out to be the worst thing in the world, because fucking damn, that was a blank check. He wasn't stupid enough to take full advantage of it right away, but there was a whole list of things he could do with ' _do what you wanted_ ' that Tommy had probably never even imagined. He let himself smile real slow, waiting until Tommy's nervous eyes darted back up to his. "That's kind of hot," he said, and understatement of the fucking century because Max could flip Tommy over and fuck him stupid right now, that's how hard he was.

"Yeah?" Tommy asked, sounding a little hoarse.

"Yeah. I mean, you already like it when I get pushy with you in bed. You don't think it'd be hot to be completely under my control?" Max leaned into Tommy's space, putting his hand on the couch for balance right between Tommy's thighs. "You wouldn't be able to say anything once you were out. You wouldn't be able to tell me to stop or say you didn't want to."

Tommy was breathing harder. He leaned in, trying to nose at Max's face to get him to turn his head to kiss, but Max pulled back, making him chase it. Tommy whined - Max did this to him, now and again. Made him say what he wanted out loud, because it made Tommy squirm.

"C'mon." Tommy practically huffed. He got desperate so fast. Max was going to love being able to take his time, play Tommy's body like he'd wanted to since he first pinned him up against the bar in that club. "Max. Kiss me?"

Max kissed him with his mouth already open, biting at Tommy's lips and, when he opened his mouth in turn, his tongue. Tommy clutched at him, hands sliding under Max's shirt, clawing at him - Max flinched. Tommy had sharp nails, and goddamn, he was going to have such a good time tonight he didn't even care for once.

"Don't you have shit to do?" Max pulled back from Tommy's clutching, panting grasp and flashed the grin that made Tommy weak in the knees. "Go do your college shit, we'll eat, you'll take your medicine. Then I'll get to do what I want with you."

Tommy sounded like he could barely suck air into his lungs. "What are you going to do?" He was staring at Max with breathless eagerness.

Max's grin got wider. "Mm. No, I'll just surprise you, I think. Maybe one time I'll film it, and you can see."

That made Tommy's mouth fall open on a shocked little noise. "God."

"Yeah? You like that?" Max took a breath, then another, and pressed the heel of his hand against his cock. He had to calm the fuck down. "Tommy, shit, you'd better do your thing or I'll wear us both out before we get to the good part."

"I'm not even going to be awake, I won't-"

"You won't know if I get you off, or if I just fuck you without caring whether you get hard. Kind of the point here."

"Jesus." Tommy's eyes were huge.

"You still okay with that?" Max leaned back, settling back on his side of the couch and picking the remote up again.

Tommy wiggled and squirmed on the other side of the couch, rubbing at the front of his jeans for a minute before he snatched his hand away like he hadn't realized what he was doing. His whole face was pink, from the backs of his ears down to the tip of his nose.

"Yeah," he finally said. Tommy was looking at the couch, not at Max. Ashamed of how much he wanted it, probably.

It wasn't Max's job to coddle him through whatever personal freakout he was having over his kinks. "Make sure you eat something first. I don't think you're supposed to take that kind of thing on an empty stomach."

Max started the show he'd been watching again, and Tommy got up to wander into the kitchen. He bumped into the door frame on the way and let out a soft little swear, looked back over his shoulder at Max like he was waiting for Max to say something else. Max pretended like he hadn't noticed, and eventually Tommy vanished into the kitchen.

It didn't take very long after that for Tommy to come back out of the kitchen and lean over the back of the couch to kiss him. "I'm, uh. Going to bed."

"I'll be there in a bit," Max said, grinning up at him and leaning up to give him another peck on the lips. Tommy returned the grin, a little shaky, but Max figured it was nerves.

He gave it another hour, just to be safe, but it was a lot harder to concentrate on following a storyline, even a simple one, when he knew what was waiting for him in the bedroom. It was also kind of hard to concentrate when he kept getting hard in his pants thinking about it.

The bedroom was dark when Max finally opened the door. Tommy was curled up under the blankets, the top of his head and one limp hand visible at the top edge of the comforter. Max pulled his shirt off and unbuttoned his pants as he crossed the room to the bathroom, looking for the prescription bottle Tommy must have left there.

He found it on the counter, a little orange bottle with a safety top. The label said _lorazepam 3mg orally once per day in the evening before sleep. Take as instructed. Do not drive or operate machinery._ On the back, the label listed a whole host of possible side effects, like over-sedation, drowsiness, and a strong warning not to mix with alcohol.

Tonight would be like a test run. Max needed to see how deeply sedated the medication would make Tommy, and how much he'd remember the next morning. He had plans beyond that, but this first night would be key.

Max kicked off his boxers as he went back into the bedroom and finally walked over to the bed. Tommy hadn't moved at all since Max came in, but that was expected - normal lights and sounds wouldn't wake him in this condition. Max just needed to see what else wouldn't wake him.

He pulled the blankets away first, a short, soft laugh escaping him when he saw that Tommy was naked, not even wearing the soft T-shirt and boxers he usually wore to bed. _Slut_ , Max thought fondly, and crawled onto the bed beside him.

The difference in temperature didn't seem to register. Tommy didn't twitch as Max pulled the last of the blankets away and shoved them down to the end of the bed. Max touched his face first, gentle and cautious, trailing his fingers over Tommy's cheek and lips. He peeled one eyelid open and held it there for a couple seconds, watching the erratic twitch of Tommy's eye, the iris rolled back and the white underside visible. His pupils were dilated and didn't react to the change in light. Max's pulse sped up. He let Tommy's eyelid fall closed and reached down to squeeze hard at the base of his own cock. He had plans, and he wasn't going to let over-eagerness ruin them.

He closed his hand around Tommy's wrist and moved the arm that was tucked up under his chin, shifting and pulling at Tommy's body until Max had him rolled over onto his back. His arms lay splayed wide where Max dropped them, his legs spread, his lips parted on soft, regular breaths. Max took a long moment to just look at him and touch, running his hands over the smooth, pale skin of Tommy's chest, the undersides of his arms, his inner thighs. Tommy's breathing didn't even change. He was completely unaware, under farther than Max had even expected.

Max slipped one finger behind Tommy's bottom teeth and pulled, opening his mouth. He ran the pad of his finger around Tommy's teeth and over his tongue, then added another, shoving far enough back to hit the soft place where his tongue met the back of his throat.

Tommy gagged, his throat constricting at the touch of Max's fingers. His mouth closed, catching Max with his teeth, and Max hissed. He wasn't biting down that hard, and he hadn't moved otherwise - an unconscious gesture, then, not anything that was going to wake him up. Max pried Tommy's mouth open and pulled his fingers out, pinching viciously at one of Tommy's nipples in retaliation. He watched, fascinated, as the muscles in Tommy's chest jumped from the pain, but the rest of him made no move to protect the tender spot. Max twisted the other nipple just to watch it happen again, greedily taking in the contrast between the flinch of his pectoral and the slack expression on Tommy's face.

The biting reflex could get annoying, but the complete lack of pain response was intoxicating. And Max could fix the biting with an open-mouth gag, something that would let him fuck Tommy's throat while he was helpless to do anything but take it.

Max raked his fingernails over the tender skin of Tommy's stomach, watching the pink lines slowly appear in their wake while Tommy lay still and unaware. His cock was soft and small between his legs, resting against his thigh. Max covered it with his palm, rubbing a little, idly wondering if Tommy could get hard with the drugs in his system. Max watched Tommy's face as he pulled his hand back and slapped, the smack sounding loud in the silent air of the bedroom. There was no change - Tommy's face was still blank with sleep, eyes closed. Max did it again, harder this time, unable to stop himself from watching Tommy's limp little dick bounce when he hit it. Max rubbed the heel of his hand over it, pinched the head between his thumb and forefinger and rolled his nail over the slit. Still no reaction besides the twitching muscles of his thighs.

God. Max slapped him again, harder than he'd intended to, feeling the sting of the blow in his own palm. Tommy's dick was pink from the abuse but hadn't gotten hard, flopping against his stomach with every blow. Max's mouth was watering, so he leaned down and sucked at the soft, unresponsive flesh. Tommy's whole cock fit easily in his mouth like this, resting on his tongue. He scraped his teeth over the shaft and bit lightly at the tender head, staring up the length of Tommy's body and moaning around the soft mouthful when he just continued to sleep peacefully. He'd wake up sore in the morning and he wouldn't know why. He'd probably think Max jacked him off, made him come while he was asleep.

Max groaned again and let the limp cock slip from his mouth. He sucked at Tommy's balls, playing with the shaft, rubbing gently instead of cruelly now, but no amount of tongue or fingers made Tommy get hard. His dick twitched against Max's fingers like it was trying, but the medication kept him soft and vulnerable.

Maybe he'd get a cock cage. If this deep of a sleep was only because Tommy's body was unused to the medication, it would be a shame to give up how small and pretty Tommy's dick was like this. A cage would keep him limp and tucked away while Max did what he wanted. He could even leave it on for Tommy to find when he woke. Max's dick jerked at the thought, Tommy blinking sleep out of his eyes and looking down in confusion, finding his cock locked away and unable to get hard, having to wait for Max to decide to let him out before he could come.

He pushed Tommy's legs farther apart by shoving at the undersides of his thighs, bending his knees until they splayed open far enough to give Max a good view of Tommy's pink hole. Max made him shave regularly, liked him smooth and wouldn't fuck him if he had stubble. Tommy gave in easily whenever Max made sex conditional on what he wanted.

Max was tempted to shove his fingers back into Tommy's mouth, to rub all over his tongue until Tommy was drooling, but he still had little imprints of Tommy's teeth. Instead he stuck them in his own mouth, getting two thoroughly wet before he pressed the tips against Tommy's asshole and shoved.

There was no resistance. Tommy was so relaxed in sleep he took both fingers all the way to the base without a twitch. Max groaned aloud, twisting his fingers, withdrawing until he could catch the rim and pull. Max would bet he could fist Tommy while he was under and Tommy wouldn't wake up for it. He could stretch Tommy's ass open until it gaped, until any come he'd filled Tommy up with leaked right out of him.

He would have plenty of chances to do that, some other time when it didn't feel like his cock was going to fall off with how hard he was. Tommy always complained when Max didn't use enough lube or spend enough time opening him up, but this time Tommy just laid there, his ass opening up nice and easy around Max's fingers with only spit to ease the way.

It made Max wonder whether he'd stay tight if he was fucked too regularly, or if he'd have to start wearing plugs because he was so stretched out and ruined. The thought made Max groan out loud, grinding against the sheets. He was going to find out exactly what Tommy could take and then he was going to push it even farther. Tommy wouldn't be able to tell him no, not when he was like this. Max was going to wreck him, and by the end of it Tommy would be so fucked up he'd stay, he'd let Max do anything he wanted.

Max had to take a long, deep breath and remind himself he had to start slow. If Tommy woke up too sore, he'd get prissy about it, and might not come back to Max's place while he was still taking the pills. He leaned over Tommy's still, motionless form to grab the nearly empty tube of lube from the bedside table. Getting his cock wet with it was torture, and Max only gave himself a couple strokes to spread it around before he pushed into Tommy's ass.

He wasn't as tight as he was when he was awake. His hole took Max's cock in like it was greedy for it, the rim stretching easily. Max stated at Tommy's face in fascination as he pushed his cock in with one long, slow thrust. Tommy's mouth was open again, saliva slipping out of the corner to pool on the pillow. Max pulled back and fucked into him again, with enough force to jostle Tommy on the bed. A huff of breath left him, like Max was fucking the air right out of him, but otherwise he didn't move.

"Fuck." Max grabbed Tommy's thighs and pulled him down to meet the next thrust. It felt too good to try and draw it out, but next time Max was going to switch between fucking and fingering Tommy for hours, until his ass was loose and wet with lube, good for nothing but taking cock. He would need that for what Max had in mind for the future. Plans were starting to form as Max's thrusts got harder, Tommy's ass hot and snug around his cock, slippery with lube but not nearly as wet as Tommy usually had him get before a fuck.

Max let go of Tommy's thighs and grabbed his jaw, opening his mouth until Max could see his pink tongue and the soft insides of his cheeks. The gag would make him perfect, open and ready to get fucked on either end all night. Max had eight hours before the pills wore off. Maybe later tonight he'd jerk off all over Tommy's face, make him wake up with come sticking his eyelashes together and the taste of cock in his mouth.

His balls pulled up tight and he groaned as he ground in deep and came hard, his eyes fixed on Tommy's open mouth. Tommy would wake up with come dripping out of his ass and still only be able to guess at what Max had done to him. That made Max's cock twitch and spurt another tiny bit of come in Tommy's insides, and Max leaned down over Tommy's body to pant for breath as he went soft. He kissed Tommy's slack, open mouth and bit at his lower lip, breath puffing over Tommy's face. He pulled out slow and easy, pushing Tommy's thighs up again so he could see come dripping out of his wet hole. Max gathered up the escaping fluid and shoved it back into Tommy's ass, then gave Tommy's cock another couple slaps for good measure, just to watch it flop against his stomach and turn pink again.

He rolled Tommy back over onto his side and arranged him in an approximation of his position before Max had fucked him, then pulled the blankets back up over them both. Tommy slept through it all, still blissfully unaware of the success of Max's test run and the filthy plans running through his mind as he drifted off with his hand cupping Tommy's ass possessively.

Max was awake the next morning when Tommy finally came out of his drug-induced sleep, his eyes opening slowly, a bleary look of soft confusion on his face. Max watched that expression morph into surprise as he shifted around, his hand going between his legs almost immediately.

"You," he gasped, bright pink. "Oh my god, Max."

"You said I could do whatever." Max leaned in and kissed him, slow and dirty, because he didn't know how else to keep the smirk off his face.

"I know, I just." Tommy squirmed, plainly feeling the come sliding out of his hole. "Wow."

"You still good?" Not that it really mattered if he wasn't, but the important thing was that Tommy thought it mattered.

Tommy didn't answer him right away. He tossed the blankets off and rolled onto his stomach so he could reach the crack of his ass better, fingers slipping through the sticky evidence of what Max had done to him while he was drugged to the gills. Max waited, trying to keep a lid on his impatience. Maybe he shouldn't have stayed in bed while Tommy woke up. Then Tommy could have had his little freakout and Max wouldn't have to coax him through it.

It turned out he didn't need to worry. "Jesus this is so hot." Tommy rolled back over to face him, his eyes flicking from Max's face down to the blankets like he couldn't quite face up to how much he wanted this. "I'm- yeah, I'm good, I'm fantastic. Will you record it next time so I can see?"

Max wondered if it was possible to die from too many boners, and pinned Tommy to the mattress, rubbing his cock on Tommy's stomach. "You want to see what you look like, or do you want to see what I do to you?"

Tommy gasped, like he hadn't thought of the fact that fucking him might not have been all that Max did. "Both?" He pushed his cock against Max's, and for a second Max was put off to feel it hard. He would have to get that cock cage. The idea of only letting Tommy get hard when Max wanted him to was looking more and more appealing.

"We'll see. Why don't you jerk off and tell me what you think I did?"

"Oh, fuck." Tommy's grabbed his dick immediately, hand moving quickly up and down the length. "You- you fucked me."

"Easy one," Max said, clicking his tongue. "Obviously I fucked you, there's come in your ass. What else?"

He watched Tommy's eyes travel down his own body, searching for any sign to interpret. "Did you make me suck you?"

"Hard to do that when you're too drugged up to suck."

Tommy groaned, his hand moving faster. "Did I get hard?"

"No," Max said, leaning in with a wide, wicked smirk. "But I played with your cock anyway. It's cute when it's all soft and small."

That hit something. Max could tell by the look in Tommy's eyes, how they went wide and nearly hurt but hot with lust at the same time. He could especially tell by the way Tommy curled up, tucked his face in the crook of Max's neck, and came in stripes over his chest.

"Max. Max holy shit."

"That was hot, baby." Max kissed at Tommy's neck until Tommy turned his head and they kissed. Tommy was panting against his mouth, wrung out and winded like he always was after an orgasm.

"You're hard." Tommy's limbs made a couple abortive jerks toward trying to coordinate motion. "I could get you off."

"Don't you have class soon? I'll be fine. I got mine last night, remember - and I'll get to do it again tonight. If I want." Max shrugged like he couldn't really give a shit about fucking Tommy or not, and watched Tommy's face fall out of the corner of his eye.

"Come on," Tommy said, his voice taking on a begging edge. "Let me suck you off. I'll swallow."

 _You will if I want you to_ , Max thought. An image of Tommy's face striped with come, more come than just one load, flashed through Max's head.

"You're going to be late," Max said, rolling off of Tommy and swinging his legs out of bed. He moved too quick for Tommy to grab him and reel him back in, grabbed his bathrobe, and slouched out into kitchen. A couple minutes later, he heard the shower running.

Max let Tommy down easy that evening when he tried to climb in Max's lap and dry hump him until Max stopped watching TV. That night, he put Tommy on his stomach, spreading his legs open as wide as he could force them. He would need a spreader bar, to keep Tommy in place for however long Max wanted his legs spread. He added that to his mental shopping list along with the gag, the cock cage, and a few different sizes of butt plugs. As he fucked Tommy like this, face down in the mattress, completely dead to the world and drooling open-mouthed onto the pillowcase, Max thought he might also want some rope, just in case.

He left bruises the next night - hickeys on the back of Tommy's neck and shoulders, finger-shaped marks around his hips and wrists. That evening, he caught Tommy staring at them, pressing his fingers against the marks on his throat and staring at Max with a desperate hunger in his eyes.

The open-mouth gag was a genius decision. With Tommy's mouth pried wide open by the wicked looking metal prongs between his teeth, Max could fuck right down his throat. It was messy - Tommy drooled everywhere, gagging occasionally when Max thrust, soaking the pillow - but it was worth it to shove his cock in until his balls sat against Tommy's chin and shoot down his throat. The next night, he pulled out and came on Tommy's face. Tommy was so turned on the next morning he pleaded for Max to touch him, face still covered in dried come, his cock so hard it leaked. Max jerked him off one-handed, barely paying attention to how he writhed and whimpered, and made Tommy lick his hand clean when he was done.

The cock cage came in the mail two days later. It was stainless steel and fitted perfectly over Tommy's soft cock. Max strapped it in place that night, staring at how the cage held Tommy's cock, how it would pinch if he tried to get hard, how the little padlock holding it together meant Tommy would have to beg him to take it off. 

Max spent hours that night playing with Tommy's hole, pushing first three, then four fingers deep inside him and pressing them against Tommy's prostate. He fitted his thumb underneath Tommy's balls and rubbed it from the outside, too, watching in rapt fascination as the limp dick locked away in its cage dripped clear fluid. The next morning, Tommy gasped when he saw what was between his legs, staring desperately at Max.

"Are you going to take it off?" he asked, quiet. He'd learned over the past week that being a whiny brat about what he wanted got him nowhere.

"I kind of like it," Max said, reaching down to cup the cage with his palm. "You can only get hard if I let you, now."

From the way Tommy's hips jerked against his hand, he wanted to get hard. He was always horny in the morning after getting fucked during the night, even the times Max wouldn't tell him what he'd done. But Tommy didn't ask to be let out of the cage and Max didn't offer, and that night when Tommy took his pill, he still had it on.

It was as good a time as any to start making recordings. Max made sure to get Tommy's caged cock in the frame when he fucked him that night, on his back with one leg tossed over Max's shoulder. The video was silent except for the sloppy sounds of lube in Tommy's ass and the slap of skin on skin. Tommy's body opened up for Max like it always did now, a smooth, easy slide that looked amazing on camera. Max pulled out to catch the money shot, coming on the cock cage and on Tommy's fucked-out ass, and then panned slowly up Tommy's naked body to his face, still fast asleep.

It took Tommy three days to figure out Max had locked him out of his laptop. "What's the new password?"

"Sorry, babe. We've got a new consultant doing audits on all the computers that have any kind of company data on them. If they ever figure out I let you use it, I could get in deep shit." Max didn't take his eyes off the TV as he spoke. Tommy was curled up on the couch next to him, his head resting on Max's shoulders.

"Oh." Tommy set the laptop aside. "That sucks. Guess I'll just use my phone."

Max had filmed Tommy a handful of times in those past three days. The videos ranged from Max fucking him to fingering him to taking the cock cage off and playing with his limp dick. He was in the middle of editing, and didn't need Tommy wondering why he was doing anything else but filming them. He was almost done re-cutting the first video to take out the times he'd swept the camera over Tommy's face - not for the version that would go public, he wanted Tommy's face in that one. The recording Tommy would see, though, would just be those long minutes of Max's dick in his ass.

He let Tommy's cock out of its cage before he cued up the edited version of the first video on the TV. Tommy watched with his hand shoved down the front of his jeans, pleading written all over his face, groaning Max's name as he stroked himself. "I need you," he whined, bucking his hips. "I want to get you off. I know you play with me all the time but I- I want to see you come, please, Max."

In the video, Max panted harshly into the camera's speaker and pulled out. Tommy made a wrecked sound when he saw Max painting his limp cock with come and stiffened, coming in his pants.

"You saw me," Max said, smirking at him. "Ready for the cage to go back on?"

"Max please," Tommy whispered. He slid down off the couch onto his knees, crawling between Max's legs. His eyes were wide and wild-looking. He set his hands on Max's thighs, but stayed sitting back on his heels, so tense he was practically shaking and waiting for Max to give him permission.

Max ignored him for a couple minutes just to watch him squirm and chew on his lips out of the corner of his eye. Then he slouched down and spread his knees wider, unbuttoning his jeans until he could pull his cock out. "Go on."

It was a little pathetic and really fucking hot at the same time, how Tommy just dove for his cock at that, cramming as much as he could fit into his mouth on the first go. His fingers clutched at Max's thighs through his jeans, and he sucked at a nearly frantic pace. Max dropped one hand to Tommy's head, grabbing a generous handful of hair and holding on while Tommy drooled and gagged around his cock. With the other hand, he grabbed the remote and turned up the volume, watching the show instead of watching the mouth on his dick. He got plenty of chances to watch himself slide down Tommy's throat. This was throwing the kid a bone, so he'd keep coming back and Max could keep making good on his plans.

Splitting his attention as he was, it took him a long time to get off. Tommy was making desperate little noises by the end, his face red, his chin wet with spit. Max bet his jaw was sore and his throat hurt, from how hard he'd been trying to deepthroat Max's cock down to the base. He was trying so hard to get Max's attention. It was almost cute, in a slutty, pathetic kind of way.

Max tightened his grip on Tommy's hair and rolled his hips up, fucking Tommy's mouth for a handful of vicious thrusts that shoved him all the way inside and made Tommy gag so hard he retched. Max held him down through it, coming down Tommy's throat with a long, satisfied sigh. He pulled Tommy off his cock by the hair and looked down at him, taking in how fucked out he looked.

"Your face is a mess. Probably want to go shower before you go to bed."

Tommy was limp in Max's hold. Max was sure the grip on his hair hurt, but he was leaning into it with his eyes closed, panting for breath. Max wondered if he'd gotten hard again while he was sucking cock.

"Thank you," Tommy croaked. He smiled, a little shaky and a lot desperate, leaning up against the hand in his hair, craning his neck. Max sighed and leaned down, giving him a quick peck on the lips. Tommy shuddered all over, like Max had done a lot more than just kiss him.

"Go get yourself cleaned up. I'll come to bed after a while."

Max watched Tommy stagger off toward the bathroom. Denying him sex - or any kind of intimate touch - while Tommy was awake had made him fragile and dependent on Max's good word. The times Max did touch him, Tommy acted like angels had descended from on high and answered all his prayers. At this rate, Max could probably talk him into anything.

Good thing, too, because with the growing library of videos of Tommy getting fucked in his sleep ready to go live to the internet at large, Max was sure he would get more than a few depraved fucks wanting to get their dick wet. The ones that were willing to pay for it might even get to fulfill their little fantasies.

A couple hours later, the apartment was quiet. Max picked up the camera, whistling cheerfully as he walked back into the bedroom, shedding his clothes as he went. The website he'd tossed together was almost ready. It just needed a few final touches, and tonight seemed like a good night to record himself fucking Tommy's mouth with the gag in.

He was going to make a killing on this sweet little ass.

**Notes for the Chapter:**

> Rape/Non-Consent archive warning is present for future chapters. This chapter contains severely dubious consent, but not outright non-consensual sexual contact. Drugged sex, medication, somnophilia, and non-consensual somnophilia tags refer to one character taking prescribed sleep assistance medication and giving his partner permission to engage in sexual contact while he is unable to withdraw consent. Consent is violated when the awake partner does not inform the sleeping partner of the sex acts performed while they were asleep. Gags, deepthroating, and face-fucking tags relate to use of an open-mouthed gag (whitehead gag or dental gag) to hold the sleeping partner's mouth open so it can be penetrated. Deepthroating and gagging also occurs when both characters are awake. Non-consensual voyeurism refers to the sleeping partner being filmed during sex and implication that the videos will be posted on the internet publicly. Abusive relationship, conditioning, and emotional manipulation tags refer to general disregard of the sleeping partner's sexual desires and limits, as well as internal narration on the part of the awake partner which clearly demonstrates lack of caring or regard for the sleeping partner's consent.


	2. Chapter 2

Tommy was a star from the minute Max hit go on the website, just like Max knew he would be. He had also mostly stopped protesting or arguing with Max about pretty much anything, not since Max touched him and got him off for being nice and obedient. He still went to classes, still only showed up at Max's place in the evening and left in the morning, but it was better. Tommy said he had more energy, and Max didn't have to put up with as much college-age bullshit. It was working out.

Max wasn't just saying that because his wallet was getting fatter from Tommy's videos, but it was honestly a big part of it. He'd started out with just a few sample videos - fingering, mostly. One short video where he fit the gag in Tommy's mouth and then smeared his cock all over his lips. Enough to whet the appetite, but not enough to give anyone the whole picture.

The teasers stayed up for a week. It was enough time to gain momentum. The email Max had set up for the site steadily got more and more queries about when subscriptions would open, when they could buy full videos, if there would be DVD releases.

If they could fuck the bottom in the videos.

He only got one or two that asked whether Tommy knew about it. Whether he had given Max permission. Max filtered through the inbox whistling, one night when he wasn't touching Tommy. He still sat in bed beside him, his leg slotted between Tommy's. The cock cage pressed against his thigh. 

He rarely took it off Tommy now, even when Tommy begged to get off so much he cried. He'd showed Tommy how he could be milked, clear fluid dribbling from his cock and relieving the pressure in his balls, but without the satisfaction of orgasm. Tommy had sobbed and clawed at the blankets, pleading brokenly for Max to please take it off, please let him come, but Max didn't, and Tommy didn't say stop.

Max sometimes wondered of Tommy even remembered he could tell Max to stop. Now that orgasms were a rare and precious thing for him, Tommy was wonderfully pliant. Max was pretty sure he'd do whatever he was asked.

Still, it was good to have insurance. The sleeping pills continued to work their magic. Tommy didn't build up a resistance, which Max took as a minor miracle. He was still limp and loose-limbed in drugged sleep every time Max fucked him. More often these nights, Max would fuck him once and then plug him up, keeping him full of come before he started rolling the cameras.

When the site opened, it was like a floodgate. Max had been expecting a response, just maybe not one so strong. He made a couple grand in a weekend from Tommy's first two full-length videos - the first one Max had ever recorded, and another where Max fucked his throat until he came all over Tommy's face. They'd both show up on the free porn sites before long, but he was already gaining subscription accounts. Those would keep him in money well enough.

Never let it be said that Max wasn't an opportunist. It got hard to keep up with the inbox before long, so Max added a location field on the contact form. He set up a filter to send locals directly to their own folder, and routinely bulk-replied or deleted the rest. They were mostly just descriptions of what they'd do to Tommy if they had him, or requests to submit similar videos for a cut of the profits. Some of them wanted to know where they were located, presumably to see whether they had a chance of fucking Tommy. But Max already had his folder of locals. He didn't need anyone else.

Max had been convinced Tommy would eventually catch on to what he was doing, but he still seemed into everything Max did to him, and really, Max didn't think he had it in him to go anywhere. Not after what Max had been conditioning him for - he craved touch all the time now, pushing into any casual hand laid on his face or his shoulder. When Max brought out the key for his cock cage he practically hyperventilated and fell on his knees without prompting; he knew he had to get Max off before he was allowed to even get hard.

Max never fucked him while he was awake anymore. He told Tommy he got enough of that when Tommy was asleep, and he could tell Tommy wanted it so bad. He would hold onto that for when he really needed a reward.

It was four days after Max uploaded the first fisting video that he got a real scare. It didn't come from Tommy, funnily enough. A couple of the videos so far had shown Tommy's face, but always with the gag in his mouth and under the fringe of his hair. This was the first video where you could get a clear shot, because Max hadn't been able to resist panning up Tommy's body as he shoved his hand deep in Tommy's ass, filming the slack mouth and utter lack of reaction.

The subject line of the email sitting in his inbox had Tommy's last name.

>   
>  From: e.surrey77@gmail.com  
>  To: admin@sleepingnaughty.com
> 
> Subject: Thomas Calahan
> 
> Tommy,
> 
> If this is what you've been doing instead of writing my papers, you're in need of some reorganization of your priorities, and maybe additional discipline if you want to avoid an investigation into your... extracurricular activities. See me in my office immediately tomorrow after class.
> 
> \- Professor Surrey 

Max stared at the email for a long time, his mouth dry. This could blow the whole thing, if this professor of Tommy's said anything to him about it. Tommy was getting more pliant, yeah, and he was more obedient than he'd ever been, but this might be the last straw even for him.

He would have to reply. He read the email again, lingering over 'additional discipline.' If the professor was emailing the site, it meant he'd been following the site, which meant he'd been jerking off to Tommy before he knew who Tommy was.

Which meant Max could fix this pretty easy. His panic was starting to subside. This could work. He had been planning his next move for a little while with the email folder of locals. This accelerated the timetable a little, but he could work with that.

>   
>  From: admin@sleepingnaughty.com  
>  To: e.surrey77@gmail.com
> 
> Subject: Re: Thomas Calahan
> 
> Professor,
> 
> You should know that Tommy isn't exactly aware of his new internet fame. He's out when these are shot. You think he seems the type to put videos of himself out on the internet?
> 
> Maybe we can work something out. If you've been watching, you know he'll take just about anything. You want in?
> 
> \- Admin

There was a chance that could backfire horribly, but Max was willing to risk that dick was a more powerful motivator than reason, nine times out of ten. It had proven true for Tommy, anyway.

Max didn't fuck Tommy that night, or film anything new. He had quite a few videos in reserve, and he was rationing the releases enough that he could probably stand not to film again for some time, in case it went sour and Professor Surrey decided to tell Tommy what was going on. Worst case scenario, he could report the site to the authorities, but Max figured he could pull it down and ditch the laptop somewhere. Then the only evidence would be Tommy himself, who'd agreed to get fucked while he was asleep in the first place. No case.

He got a reply the next night that laid his worries to rest. Professor Surrey was exactly the kind of dirty old man who'd jump at a chance to fuck one of his students, even if the student in question was drugged at the time. He didn't want his face to be on film, but he didn't object to being filmed in general. That was good - it would give Max some variety for the site.

Besides, it would be a little test for what was going to come later.

Max set up a time. Late on a Friday night, Professor Surrey knocked on the apartment door, and Max went to let him in.

Surrey wasn't as old as Max expected. He looked like he was probably in his fifties. His beard had gone grey, but he had some brown left in his hair. He shook Max's hand like this was just another business meeting, and Max stepped aside to let him in.

"Tommy's already out," Max said. "He usually takes his sleeping medication pretty early. By now he won't wake up for anything."

"That's fortuitous for you," Surrey said. He looked around the apartment for a moment, his eyes lingering on the bedroom door. "What is it you expect in return for this?"

Max shoved his hands in his pockets and shrugged. "Normally I'd charge, you know. But I bet you've been wanting that cute ass on your dick since you first saw him. Doesn't he just make you want to see how much he can take?"

"He has a certain eager-to-please nature, yes," Surrey said. "It's why I thought initially he must have been aware of what was happening. I assumed a convincing enough partner would likely be able to get him to do anything."

"Pretty much, yeah." Max tipped his head toward the bedroom. "You want to go ahead? I haven't fucked him yet tonight."

"Would you?" Surrey followed Max into the bedroom, loosening his tie. "Part of the appeal is the sloppy seconds."

"Man who knows what he wants," Max said, giving Surrey a sharp grin. "I can respect that. Anything else?"

"I'll have his mouth while you're fucking him, if that's all right." Surrey stopped in the middle of pulling his tie off and inhaled audibly.

It had been so long since Max had gotten Tommy in bed that he sometimes forgot how pretty the kid was. He was slender, his back dotted with beauty marks, his hair curling around his ears and the nape of his neck. Max had put him on his stomach and spread his legs, so Surrey could see Tommy's cock cage hanging between his legs.

Surrey stepped closer to the bed slowly. "Can I touch him?"

"You can do whatever you want with him. Like I said, he's out."

Surrey's shirt was open down the front, his tie discarded. He was pudgy around the middle and his chest was covered in grey hair - not the look Max usually went for, but his cock started to thicken up anyway when Surrey grabbed a handful of Tommy's ass in both hands and squeezed. Surrey leaned down and mouthed at the back of Tommy's neck, biting at his shoulders. He grabbed Tommy's cock, rubbing at the soft skin between the metal of the cage.

"He doesn't feel anything, or remember when he's awake?" Surrey asked. His eyes were fixed on Tommy's face.

"Never has. He can figure out what I do to him sometimes, but he's not very creative. I don't think he's figured out I fuck his mouth. Or the fisting."

"Fuck." Surrey bit the soft, yielding flesh of Tommy's ass, sucking until he left a mark. He pulled back, watching Tommy's face, and then pressed his thumb down on the bruise. Tommy didn't flinch, though his lips parted in his sleep. "Where is that gag you use?"

Max pulled out the lockbox from under the bed. It kept most of the toys Tommy didn't know Max used on him, as well as the camera equipment that would have looked suspicious hanging around the apartment.

"Get that in while I get set up."

"You're going to start filming now?" Surrey took the gag from Max, his eyebrows drawn together.

"I said I'd keep your face out of it, and I will. But I'm not going to pass up an opportunity to film him getting stuffed on both ends, you get me?"

Surrey swallowed thickly. Max could see his dick through his slacks, not completely hard yet but definitely getting there. Surrey turned to fit the gag in Tommy's mouth, and Max started setting up the tripod. He was an older guy, so Max figured he probably had stamina. Max was looking forward to getting a damn good video out of this.

When he finally had everything set up and hit record, Surrey was playing with Tommy's mouth. He had his fingers on Tommy's tongue, stroking over the wet surface of it. Max focused the camera on it, zooming in on Surrey's fingers poking at Tommy's cheeks, pulling at his teeth, and rubbing over his tongue. There was something hot about the way Surrey was playing around without even getting his dick out. Max squeezed his own cock through his jeans.

"Everything ready?" Surrey asked, finally stripping his shirt off and tossing it aside. He unbuckled his pants, the buckle clinking in the dark quiet of the bedroom.

"Yeah," Max said, pulling his own T-shirt off over his head. Surrey looked up at him, his eyes traveling over Max's chest. Max felt like scowling - he wasn't here for Surrey to stare at - but he held it back, biting the inside of his cheek. "Ready whenever you are."

Max climbed onto the bed between Tommy's legs. He spread Tommy's ass open for the camera, pressing his thumb against Tommy's slick hole. Max had lubed him up before Surrey arrived, not wanting to waste time on it and not wanting to risk that Surrey would want to fuck Tommy dry. Max had worked really hard to keep Tommy in good condition. He'd be worthless if he was ruined.

Surrey pulled his cock out and eased it into Tommy's mouth. He didn't give him much more than the head, rubbing it around the inside of Tommy's cheeks like he had with his fingers. He wasn't really fucking Tommy's mouth, just playing with it.

Max wasn't so patient. He pushed his dick into Tommy's ass and started fucking him right away, bouncing his limp body on the mattress. He had a lot of practice keeping his own legs out of the way of the camera by now. He'd had to delete too many videos because he got too into it and forgot about filming angles.

His thrusts jostled Tommy onto Surrey's cock, driving it deeper. Surrey was clutching at Tommy's hair now, pushing his mouth down. A soft gagging noise interrupted the sound of skin on skin, and Surrey drew back, glancing up at Max.

"Nothing to worry about," Max grunted. Tommy was slick and loose, a sloppy fuck when he was out like this, and it always made Max come faster than he'd intended. "Fuck his throat if you want."

"He won't notice?" Surrey asked, but he shoved his dick back into Tommy's mouth, pushing Tommy's head down on it until he gagged again, drool spilling out of his stretched-open mouth.

"He'll just think I did it. He knows about that part." Max would have to cut the audio and edit it to get their voices out. At least he'd still have some of Tommy's gagging he could use, and he could do a split screen of him getting stuffed at both ends.

It was hot, watching Tommy's mouth get fucked from this angle. Surrey was slow about it, trying to draw it out and probably trying to make sure he didn't come before he got to fuck Tommy's ass. He would pull his dick out and rub it all over Tommy's cheeks and open mouth, press the head against his tongue, then push all the way back in until Tommy was choking on it. Then he'd pull out and do it all over again. Tommy had spit all over his face and his closed eyes were watering, tears collecting on his lashes. His body wanted to fight it, but he just couldn't, not while he was sedated by the pills.

It was that thought that made Max come, gripping Tommy's hips hard enough to leave bruises and grinding deep inside him. Visible come shots might sell better, but Max wasn't going to ruin a good fuck just to jerk off for the last part of it, even if Tommy's hole did look pretty when it was a mess. He grunted as he came, breathing hard, and stayed there for a minute, fucking Tommy slow until his dick got too sensitive.

When he pulled out, a little stream of come followed, dripping down the backs of Tommy's balls. Max grabbed the cheeks of his ass and spread them open so the camera could see how his hole gaped a little.

"You wanted sloppy seconds," Max said, with a satisfied slap to Tommy's ass. "Done playing with his mouth?"

Surrey couldn't take his eyes off Tommy's mouth, thrusting lazily between the metal prongs of the gag. When he finally tore his eyes away, it was to drag them down Tommy's naked back to his ass.

"His mouth is so good," Surrey panted, looking down at his cock again.

"Hey, you want to come in his mouth or all over his face, be my guest. You really should have his ass though. It's better."

Surrey groaned. "Impossible," he said, but he pulled out anyway, his cock swinging between his legs as he crawled down the length of the bed to settle where Max had been a few moments before.

Max took the camera off the tripod and moved to get a better angle. Surrey had a nice cock, thick and well-proportioned, stretching Tommy's hole a little wider than Max had. Max was at just the right angle to see strings of come on Surrey's cock as he pulled out and thrust in deep and slow. The noise that came from Tommy's body was wet and obscene. Surrey moaned, leaning down on his elbows until his whole body was covering Tommy's.

"God," Surrey gasped. "You lucky son of a bitch, it's perfect. He's perfect. He lets you do this?"

"He lets me do a lot more when he's awake. The cage doesn't come off." Max heard Surrey groan like he was dying and smirked. "Yeah, every time you see him in class, he's all caged up. He doesn't even beg to come anymore, he just wants my dick in his ass. Maybe we can play this right and he'll spread his legs for you, too. You want to fuck him in your office? You could bend him over the desk and fuck him, come in his ass and plug him up before you send him home. He'd probably be so grateful he cried. I only let him blow me."

"That is filthy and depraved," Surrey said, definite admiration in his voice. "You've done beautiful work with him."

"Well, those pills work miracles. Quiet on set, now. Let's get the money shot."

Max zoomed out and panned slowly around, making sure to catch the side where Surrey had his face turned away. Tommy's mouth was still stretched wide around the gag, the pillow under his face wet with saliva. He zoomed the camera in on where Surrey was pounding Tommy's ass like he didn't think he'd get to fuck anyone ever again. It was messy and wet, lube and come dripping down Tommy's balls as Surrey fucked it out of him with every thrust. 

"You're a mess," Max murmured into the camera. "Pretty little slut fucked on both ends."

Surrey grunted, shuddered, and came with his hips jerking. He stayed there, panting and balls-deep in Tommy's ass, until Max thought he would have to say something. Finally, he pulled out, more come squelching out of Tommy's used hole and dripping onto the sheets.

"Spread him open," Max said. Surrey didn't just grab Tommy's asscheeks, he hooked his thumbs in Tommy's loose ass and opened him back up, come still leaking out of him. "Look at that slutty hole. I bet he could take more."

Surrey worked the first finger of each hand in beside his thumbs. Tommy's hole stretched open like it was made to take whatever they put in it. Max looked around for something to plug him up with and grabbed the beer he'd been drinking out of earlier. He chugged the rest of it and handed the empty bottle to Surrey.

"Stick it up his ass, keep some of that come in him."

"Fuck," Surrey rasped. He dragged the bottom of the bottle through the mess of come on the sheets. He pulled his fingers free and pressed the glass against Tommy's fucked-out hole, pushing until the wide, round end of the bottle finally breached him. Surrey pushed until about half of it was inside, stopping short of where the bottle started to narrow into the neck. Then he pulled it out slowly, twisting, and worked it back in.

"Yeah," Max said. "That hole isn't good for anything but fucking now, is it?"

He panned up Tommy's body one more time, zooming in on his closed eyes, and then turned the camera off.

"You're done?" Surrey asked, still fucking Tommy with the bottle, watching the stretched rim of his hole cling to the glass.

"Yeah, it's about time I pack it up. I have to get the video off the camera, put everything away. He's still got to wake up and go to class in the morning." Max considered Tommy's stuffed-full hole. "I might leave that in him until he wakes up. I haven't let him wake up plugged yet."

"You're a special kind of depraved," Surrey said. He left Tommy on the bed, bottle stuck halfway in his ass, and went to wash his hands in the bathroom. Max hooked up the camera equipment up to his laptop to start the process of downloading. This video would take weeks to hit the site; he needed to edit, and he also didn't want to open the floodgates to people who wanted to make an appearance like Surrey. Not yet.

He barely paid attention when Surrey left, calling a distracted goodbye. He looked over at Tommy again, at the purpling bruise Surrey had left on Tommy's ass and the bottle stuffed in his hole. He should really change that out for a plug; as good as Tommy looked used like this, it might be a little much for his first time waking up stuffed with something. Max sighed, getting up from his chair, but his slow progression on Tommy had worked so far. He wasn't about to screw it up because his dick got the better of him.

The bottle came out of Tommy's ass streaked with come, his hole swollen and gaping. Max wiped it off on Tommy's thigh, then rummaged through the toybox for the medium-sized plug. His ass was too loose for the smallest size. Max pushed the come that had dribbled out of him back into his hole and pushed the plug in after it.

For once, he made himself wake up before Tommy. Usually, it was Tommy's whimpering and squirming that woke him, as he felt everything Max had done to him in the night. This time, Max really wanted to see his face when he felt the plug.

It wasn't disappointing. Tommy always woke up slowly from the pills, starting by shifting around the bed, then rolling over and kicking the blankets off. His eyelids fluttered open as he turned onto his back.

"Oh," he gasped, reaching down past the cock cage to feel the base of the plug.

"I fucked you twice last night," Max whispered in his ear, lips soft against his skin. "Filled you up and plugged you to keep it inside. You like it when your ass is full of come?"

"Yes, Max, I--" Tommy pushed at the base of the plug and groaned, arching on the bed. "Can I come?"

"Not right now, but you can earn it."

Tommy licked his lips. Usually when Max said _earn it_ he did mean Tommy sucking his dick, but not this time.

"I think that slutty hole needs more come in it," Max said, pulling Tommy's thigh up until he could grab the base of the plug, pulling it out just enough to stretch the rim of Tommy's asshole and pushing it back in. "My dick is tired, though. Guess you're going to have to find someone else to give you another load."

Tommy froze, his mouth open in surprise. Max made himself keep breathing normally, twisting the plug inside Tommy, casually fucking him with the toy to hopefully chase any doubts out of his mind. Tommy hadn't been fucked while he was awake in a long time, and Max knew he was probably aching for it.

"You want me to go find someone else to fuck me?" he asked, disbelief in his voice.

"You want it so bad, baby," Max said. "Always begging me to stick my dick in you. If I can't give you what you need, you should be able to go find it somewhere else. I bet you can find someone kinky enough to fuck you with someone else's come in your ass."

Tommy groaned, his cock swelling in its cage, red and pressing against the silver metal. His thighs were twitching, his hips rocking back against Max's hand as Max played with the toy. His face was flushed red, his mouth open on little panting breaths.

"And if I do it, you'll take the cage off and let me come?" Tommy asked, breathless.

Fucking perfect.

"If you want, I'll even finger you while I do it. Get something in that greedy ass so you can come properly."

"Max, _yes_ ," Tommy groaned, throwing his head to the side. His eyes landed on the alarm clock and he groaned again, an entirely different tenor. "Fuck, I'm going to be late to class."

"Go on," Max said, slapping the inside of his thigh.

After Tommy had left the apartment, Max logged into his site's email.

>   
>  From: admin@sleepingnaughty.com  
>  To: e.surrey77@gmail.com
> 
> Subject: Sloppier seconds
> 
> Professor,
> 
> I'm sending him your way. He's supposed to get fucked today before he can come.
> 
> It'd be nice if you could film it.
> 
> \- Max

It took longer than Max expected to get a reply. Maybe the professor taught a class early in the morning. Max knew that Professor Surrey wasn't Tommy's first class, because Tommy had complained about his schedule often enough. Finally, about the time he'd almost given up and gotten ready to do some actual work, his inbox showed a new message.

>   
>  From: e.surrey77@gmail.com  
>  To: admin@sleepingnaughty.com
> 
> Subject: Sloppier seconds
> 
> I can do better than that. Skype burnergenie77 at 3:30. I'm having Tommy come in for office hours.
> 
> \- Professor 

Max grinned to himself. An hour and a half to spare to download Skype, make a new burner account, and find some kind of screen recording software. He had a feeling he was going to want this video for posterity.

He called right on time, the cheerful burble of Skype's ringtone an innocent counterpoint to what was about to happen. Surrey connected the call, and for a moment all Max saw was the top of his head.

"Bear with me a moment," Surrey said, sounding tinny and far away. The video swung down, giving him a closeup view of Surrey's beard. Some further tinkering and it was zoomed in on the desk in the middle of the office.

The professor's office was a wreck, little piles of papers and books strewn around. It was cramped. The little camera he'd set up on what was probably another crowded bookshelf got most of the room, with a blank space off behind the camera angle that Max assumed was the door.

"He'll be here soon. Mute your end of the sound, and we'll give you a show."

"You're pretty good with this stuff," Max said, impressed despite himself.

"I'm not ancient," Surrey said, shaking his head at the camera. Then he settled into the chair behind the desk and by all appearances got to work. Max muted his microphone and watched, waiting for Tommy to arrive before he cued up the screen recording software.

The soft tap on the door came about fifteen minutes later. Max sat up in his chair and hit record.

"Professor?"

"Thomas, yes, come in. Close the door behind you. Sit."

Tommy looked pretty worse for wear. He wasn't used to walking around plugged yet, and the medium plug would tease inside of him in a way that had to be maddening with the cage on. He sat carefully in the chair. Max could only see the back of his head, but he watched a flash of hunger pass over Surrey's face through the grainy camera feed.

"We need to talk about your performance in class, Thomas," Surrey said. "It's been rather lackluster. You consistently arrive just at or just past the start of classtime. You fidget. You daydream. In short, you're a distraction to yourself and to everyone around you."

"Professor," Tommy mumbled, the half-formed start of a protest. His shoulders were hunched.

"Don't interrupt," Surrey said, severe. "If you were a more attentive student, I would consider offering extra credit work to make up for the defecit in your classwork. As it is, I'm afraid I might have to fail you."

Tommy jolted in his chair, a noise coming out of his throat that was practically a whimper.

"Professor, please," he said, sounding desperate. "I'll do the extra work, I'll make up the grade. Give me a chance."

"It's rather late in the semester. I'm afraid the chance to make up your performance is well behind you. Perhaps you should have paid more attention in class and been less distracted by whatever it is that has you staring into the distance during my lectures." Professor Surrey stood, like he was about to walk around the desk and shake Tommy's hand to dismiss him.

"Professor Surrey," Tommy said, jumping up from his own chair. "I can't fail this class, it's not offered for another two semesters. I won't be able to graduate, I-- please, please, I'll do anything."

Those three magic words. _I'll do anything_. They made Surrey pause, and they made Max slide his hand into his sweatpants, cupping his dick. This show was about to get on the road.

"Anything, Thomas?" Surrey asked, leaning against the side of his desk. "That's a broad offer."

"Please," Tommy reiterated, and Max could tell from what little of Tommy's profile he could see that he hadn't thought about what it could sound like yet. There was a shivering, ancipatory pause, while Surrey held Tommy's eyes like he was waiting for Tommy to get down on his knees and beg.

"Lock the door, then," Surrey said, dragging the other chair away from the desk.

Tommy looked from him to the door. Max could read the dawning understanding on his face. He swallowed, then he walked out of view momentarily. The speaker wasn't sensitive enough to hear the lock click on the door, but Tommy shuffled hesitantly back into view a moment later.

"Bend over the desk. On your elbows," Surrey ordered. Tommy's lip trembled, and for a moment Max thought he would refuse, but he took the orders. He bent over the desk, his ass stuck out toward the camera, leaned down on his elbows so his spine sloped in a pretty curve.

"I think you need to be taught some discipline," Surrey said, his voice light and conversational. Tommy squirmed as Surrey unbuttoned his jeans and worked them down around his thighs, pausing when they slid over the cheeks of his ass and revealed the plug.

"What's this?" he asked, pressing hard against the base of the plug with his thumb. "Someone is keeping this slutty hole open and ready to fuck."

"M-my boyfriend," Tommy stuttered. "He put it in me this morning."

"And you were wearing it in class?" Surrey clicked his tongue. "No wonder you can't pay attention. Kick out of your shoes, get those off and spread your legs."

Tommy hustled to comply, shoving at the heels of his shoes with his toes until both popped off, then wiggling his pants down his legs, finally pulling his socks off with his toes and shifting his legs wider. His head hung low on his elbows. The only problem with a stationary camera was that Max wouldn't be able to see his face. He looked good when he was desperate and embarrassed. With a deep breath, Tommy shifted his legs apart.

"Well, now," Surrey said, pretending to be surprised by the presence of the cock cage. He reached out and cupped Tommy's sensitive, swollen balls in his palm, pressing on them just a little. Tommy's thighs shuddered and he gasped. "Looks like someone else thinks your discipline needs work. Your boyfriend again?"

"Yes," Tommy whispered.

Surrey squeezed, making Tommy yelp. "'Sir,' Thomas. Be polite."

"Yes sir," Tommy said, his voice a little high. Surrey released his balls, rubbing at the angry red shaft pinched behind metal rings. He was playing with Tommy's caged cock the way he hadn't been able to last night.

"I take it you aren't allowed to come unless you do something very special, is that how it works?" Surrey asked. He was stroking the soft skin of Tommy's ass, the backs of his thighs, like he was petting the skittishness out of him.

"Yes sir, I have to," Tommy paused and gulped, "I have to have another load of come in my ass."

"Another?" Surrey asked, feigning surprise again. He squeezed Tommy's asscheek this time. "How many do you have in there right now, slut?"

"Two." Tommy sounded like he might die from the shame of it. Max wrapped his hand around his hard cock, stroking ever so slowly. Surrey's hand moved suddenly, from squeezing to a sharp smack, making Tommy yelp, his thighs and the cheeks of his ass tensing. He would be squeezing down on the plug, too, making it rub harder against his prostate.

"Manners," Surrey said sharply.

"Sir! Two, sir!" Tommy whimpered. "Will-- are you going to fuck me, sir?"

"I might," Surrey said, sounding careless. "I think the most important thing is to correct your distracting behavior, though, so I'm going to spank you. Thank me for using my hand instead of a paddle."

"Thank you, sir," Tommy said, sounding miserable. Surrey held out his palm in front of Tommy's face. Tommy had to stretch up on his tiptoes and strain to kiss it.

"You can be a good boy," Surrey observed, and Max could see the red flush down Tommy's back from here. He was so easy for praise. "Let's remind you why you should be."

Surrey was merciless with the spanking. Max had never done this to Tommy before. He'd been afraid it would be too much, too fast. But Tommy was put in too desperate a position by Surrey's threat to fail him, and he couldn't refuse. He just wiggled and cried out into his arms and shuddered as Surrey's steady, skin-on-skin blows turned his ass from pale peach, to pink, to red. 

The blows from Surrey's hand were even and hard, rocking Tommy up on his toes and leaving brief, darker handprints before the next slap made Tommy's skin bloom with color again. Max was jerking himself in earnest now, but he didn't quite reach the point of coming before the spanking came to an end. Surrey smoothed his hand over the reddened cheeks, squeezing. The only sound on the camera feed was Tommy sobbing. The only sound in Max's bedroom was the slick sound of his hand on his dick.

"Did that hurt?" Surrey asked, sounding almost contrite. "Your ass is so warm and red now. Every time you sit down in class you'll remember that you should be paying attention. Maybe we should make this a regular thing, hm? We might need to maintain your discipline."

"It hurts, sir," Tommy cried, his voice trembling, his shoulders shaking.

"Yes, of course it does. It's supposed to, Thomas. It hurts so you can remember to do better." Surrey's hand crept between the cheeks of Tommy's ass, pulling on the base of the plug. "You need me to fill you up so you can do what your boyfriend said, don't you? Come home with your slutty hole wet with another man's come?"

They'd both already come in Tommy last night, but Max had to respect Surrey's commitment to deniability.

"Yes sir," Tommy moaned, shifting his feet so he could spread his legs wider.

"You'll have to ask me politely for it," Surrey said. "Let's see if you still remember how to ask your professor something, since your class participation has been so abysmal."

"Professor Surrey," Tommy said, his voice quavering. "Will you please fuck me?"

"Is that all you want me to do, just fuck you? I think I'll come on my handiwork here."

"No!" Tommy yelped, earning another hard slap that made him cry out. "Sir, no, I need you to come in me. Please, fuck me and come in me."

"Tell me where you want me to come again," Surrey said. "Be descriptive. Your essays always did lack a certain amount of imagination."

Tommy twisted to look over his shoulder, an adorably confused look on his face. His tongue came out to wet his lips, and he whimpered again when Surrey started to draw the plug out of him, his rim stretching around the silicone.

"Please... come in my slut hole?" Tommy asked, sounding unsure. Surrey, though, patted him on the reddened asscheek for it.

"It's a start," he said, setting the plug carefully on the desk. "Hold yourself open for me, Thomas."

Tommy reached back, his chest flat on the desk, up on his tiptoes, and winced as he grabbed a double handful of his painful, probably throbbing ass, spreading the cheeks open to bare his hole. A little tiny drip of come was escaping. Surrey lined his cock up and pushed it back in with careful, inch by inch thrusts. He hadn't lubed up. He was using their come from the night before to ease his way, and from the scrunched look on Tommy's face, it wasn't quite enough.

"Take it," Surrey said, his hand coming up to grip the back of Tommy's neck. "You asked me to fill your slut hole up with come, not to make you enjoy it."

Tommy's eyes slid closed and he shivered, biting his lip to contain the little hurt noises he made while Surrey pushed into him. He didn't fuck Tommy quite as hard as he'd done last night, maybe afraid of what Max might do if Tommy was actually damaged. The webcam didn't give Max a very good view, but he could imagine how it looked. Tommy's hole would be puffy and red, fucked out, with strings of last night's come clinging to Surrey's dick. Tommy would be red and swollen in his cage, his soft little cock swinging while Surrey fucked him. Tommy still held himself open, his chest jostled on Surrey's desk, his own fingers digging into the red flesh of his ass.

"Please sir," he begged, sounding pathetic and wretched. "Professor, please, come in me. F-fill up my slutty ass."

"Do you want the whole floor to hear you?" Surrey panted, reaching out to grab the back of Tommy's neck again. He forced Tommy's face into his desk, mashing it against a stack of papers. "I'll finish with you when I'm ready."

Max could just barely get a glimpse of tears rolling down Tommy's cheeks. He grunted, coming in his sweatpants, toes curling against the carpet. The orgasm shot through him, leaving him wrung out and panting while he watched the last couple minutes of Surrey riding Tommy's ass before he shoved in deep and came.

He plugged Tommy up again and gave him one last swat on the ass.

"Fix your clothes," Surrey said. "Take a tissue and wipe your face off. The next time I see you in class, you'd better be ready to pay attention or suffer more consequences."

"Yes, sir," Tommy said, meek, looking at the floor.

"You can leave now, Thomas," Surrey said, and Tommy practically bolted.

When the door swung shut behind him, Max unmuted the mic.

"Fucking good work," he said. "You're good with him."

"Boys like Tommy take a heavy hand," Surrey said, breezily, like he had experience with this kind of thing. "If you're interested, we could make some kind of standing arrangement."

Max, withdrawing his sticky hand from his pants, promised nothing.

"We're even," he said. "I've got the recording of this session. Mutually assured destruction."

Surrey inclined his head toward the camera. "I assumed you would. I have no intention of turning you in, you know. I'd lose access to Tommy, more than likely. He's a sweet enough fuck to want to keep around."

Even with all the annoyance Tommy caused, Max had to admit it was a fair assessment. He disconnected the Skype call and waited for Tommy to show.

When he did, he was in a mood like Max had never seen him. He shuffled through the door, barely looked at Max. He was wincing when he walked and when he sat down. Max let him fiddle with the hem of his shirt in silence for a minute before he walked up and pushed his fingers into Tommy's hair, forcing his head back.

"Did you earn what you wanted?" he asked. If this was Tommy feeling guilty for spreading his legs for someone else, Max needed to nip that in the bud. Tommy needed to get used to that.

"Yeah," Tommy said softly, dropping his eyes. "My, um. My professor."

"Kinky," Max said, smirking. "Was he good?"

Tommy fidgeted in his chair. "I haven't been doing so well in his class. He was pretty serious about making sure that didn't happen again, so."

Max made sure to let the greed creep into his face.

"Let me see," he said, stepping back.

Tommy stood up slowly, taking off his shirt along with his pants and underwear. Max had gotten him used to being naked around the apartment, because Max liked to touch him as much as possible. Tommy took a deep breath and turned around, bending over so Max could see.

Max let out a low whistle. Tommy's ass was still bright red, darker in some places like the heel of Surrey's hand might have left a bruise. He stepped closer, reaching out to touch. He could feel the heat rising off Tommy's skin from half an inch away.

"He did a number on you, huh," Max said lowly, before he finally made contact with Tommy's ass and squeezed. "He still fucked you, right? Gave you a load right where I told you to take one?"

"Yeah," Tommy nodded, his voice trembling a little.

"Then I think you've earned your reward, yeah? Sit back down. Legs over the arms. Scoot up like this."

Tommy made a pained face as he scooted forward until his ass was just hanging off the cushion of the armchair. Max considered him, sprawled out in the chair, lean and flushed, the hard metal of the cage drawing the eye.

Max pulled the tiny key from his pocket and unlocked the mechanism, drawing the metal rings away from the shaft of Tommy's cock. Immediately, blood surged to his dick. Max watched as he got hard, so hard his cock was red with it, already dripping before Max had even touched him. Tommy was breathing so hard just looking at his own erection. It had been weeks since the cage had come off.

"I'm going to take your plug out, now, and make sure you weren't lying to me. Don't make a mess."

Tommy clenching down around the plug made it harder for Max to pull it out, especially with how raw and sensitive his hole was. Max kept going, relentless, until Tommy's body finally surrendered it, the widest portion popping out with a sloppy sound.

"You gorgeous little whore," Max said, admiring, as a fresh glob of come dripped from Tommy's hole. He shoved it back in, two fingers sinking easily in Tommy's fucked-out ass. "You bend over just as good for someone else as you do for me."

Before Tommy could say anything, Max twisted his fingers until he was rubbing Tommy's prostate and started to jack his dick with the other hand. Tommy came alive, shuddering and bucking into Max's grip, punched-out sounds of desperate pleasure huffing out of his chest.

"Max," he gasped. "Max, please, oh god, I'm gonna come so fast."

"Then you go back in your cage, babe," Max said. "Your cock looks prettier when it's all locked up. Come on, come so I can put you back in."

Tommy made an agonized sound. He didn't want to be put pack in the cage, but Max wasn't playing fair. He circled his fingers gently on Tommy's prostate, jerked him off brutal and efficient, and in the end Tommy was coming all over his chest, streaking his nipple white.

Max leaned in and bit that one while he kept pulling on Tommy's cock. His asshole squeezzed and spasmed around Max's fingers as he kept pushing on Tommy's prostate. Tommy's feet kicked out, his hands scrabbling at the chair, tears filling his eyes.

"Max!" Tommy sobbed, shuddered into a dry, overstimulated orgasm, and started crying in earnest when Max didn't stop working his hands. Tommy didn't have enough in him for another orgasm, but Max was able to squeeze a long drip of clear fluid from the head of Tommy's cock before pulling his fingers free.

He reached for the cage again, and Tommy was too dazed, tired, and fucked-out to protest. He tucked Tommy's sticky cock back into the cage, locked it up, and stood. He stretched, full-body, and yawned.

"You should go get showered. It's time for your medicine soon, and the last time you showered after you took the pill, you almost killed yourself falling in there."

Tommy's unfocused gaze landed on Max, and he blinked slowly, like he knew he was suppoed to understand what those words meant, but he just didn't. After a minute, he slowly pushed himself up from the chair. Come began to drip down his thighs as he staggered off to the bathroom.

Max had, at least, successfully driven any shame or second-guessing out of his head. Shame and embarrassment were irrelevant at this stage of the game. He needed to break Tommy of that for good.

Luckily, he had an idea of how to do it. He just needed a little more time, and then Tommy would be the perfect little whore while he was passed out and anyone could take him.

**Notes for the Chapter:**

> Additional warning tags have been added. Non-Consensual Somnophilia tag added due to the unconscious character being fucked by someone he has no knowledge of and did not consent to have sexual contact with. This chapter adds a manipulative and coercive scene between a student and a professor. Spanking tag is for bare-handed spanking over the professor's desk. Verbal humiliation tag has been added for the use of "slut" and "whore".


End file.
